For donations of goods, one would need a letter from the organization acknowledging the donation. That might be one way to legitimize for the individual. (And if you do this you'd still need to account for the inflow and the offsetting expense if you're going to legitimize this).

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You'd probably want to account for this as a restricted donation.

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Which brings up the best practice here. Have him make the gift to the non-profit, with the restriction that it's to be used only for the payment of that bill.

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bear with me a moment and let me see if I can find a Revenue Procedure or Tax court case. The code is silent here, other than the fact that the cost must be out of pocket, which it is.

I also see this, "gift to or for the use of.." in various secondary sources (Master Tax Guide, ALR) being quoted as the reason that an executive or other related party of the non-profit can deduct bills paid on behalf of the charity.

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You're good to go here. But two "heads-up;"

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Never give a donor tax advice about what's deductible, and as I already mentioned, DO give a letter of acknowledgement, in the event the donor is audited. (Said differently, you should acknowledge the gift, but not provide tax advice about the tax deductibility of the gift)

Please let me know if you have ANY questions at all, before rating me.

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I hope you’ll rate me (using those stars, or faces on your screen, by clicking submit) based on thoroughness and accuracy, rather than any good news / bad news content.

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Otherwise I’ll receive no compensation for the work here at all, from JustAnswer.

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Thank you!

Lane

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I hold a law degree, with concentration in Tax Law, Estate law & Corporate law, an MBA, with specialization in finance a BBA, and CFP & CRPS (Chartered Retirement Plans Specialist) designations, as well - I’ve been providing financial, Social Security/Medicare, estate, corporate, non-profit, and tax advice, to clients on three continents since 1986.

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Disclaimer: Information in questions, answers, and other posts on this site ("Posts") comes from individual users, not JustAnswer; JustAnswer is not responsible for Posts. Posts are for general information, are not intended to substitute for informed professional advice (medical, legal, veterinary, financial, etc.), or to establish a professional-client relationship. The site and services are provided "as is" with no warranty or representations by JustAnswer regarding the qualifications of Experts. To see what credentials have been verified by a third-party service, please click on the "Verified" symbol in some Experts' profiles. JustAnswer is not intended or designed for EMERGENCY questions which should be directed immediately by telephone or in-person to qualified professionals.